Problem: Although ethyl bromide and isobutyl bromide are both primary halides, ethyl bromide undergoes SN2 reactions more than 10 times faster than isobutyl bromide does. When each compound is treated with a strong base/nucleophile (EtO-), isobutyl bromide gives a greater yield of elimination products than substitution products, whereas with ethyl bromide this behavior is reversed. What factor accounts for these results?  

🤓 Based on our data, we think this question is relevant for Professor Hopkins' class at UW-SEATTLE.

FREE Expert Solution
Problem Details

Although ethyl bromide and isobutyl bromide are both primary halides, ethyl bromide undergoes SN2 reactions more than 10 times faster than isobutyl bromide does. When each compound is treated with a strong base/nucleophile (EtO-), isobutyl bromide gives a greater yield of elimination products than substitution products, whereas with ethyl bromide this behavior is reversed. What factor accounts for these results?
 

Frequently Asked Questions

What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) concept. You can view video lessons to learn SN1 SN2 E1 E2 Chart (Big Daddy Flowchart). Or if you need more SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) practice, you can also practice SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) practice problems.

What is the difficulty of this problem?

Our tutors rated the difficulty ofAlthough ethyl bromide and isobutyl bromide are both primary...as high difficulty.

How long does this problem take to solve?

Our expert Organic tutor, Chris took 3 minutes and 36 seconds to solve this problem. You can follow their steps in the video explanation above.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Hopkins' class at UW-SEATTLE.

What textbook is this problem found in?

Our data indicates that this problem or a close variation was asked in Organic Chemistry - Solomons 10th Edition. You can also practice Organic Chemistry - Solomons 10th Edition practice problems.